Hydrogen Peroxide → HCID 71539628, compound

HRID 1466216Notes

Reaction equation

HRID 1466216 reaction equation
[CH:1]1([CH2:4][N:5]([CH2:45][CH:46]2[CH2:48][CH2:47]2)[C:6]2[N:11]=[C:10]3[N:12]([C:16]([CH3:19])([CH3:18])[CH3:17])[N:13]=[C:14]([CH3:15])[C:9]3=[CH:8][C:7]=2[CH2:20][N:21]([CH2:30][C:31]2[CH:36]=[C:35]([C:37]([F:40])([F:39])[F:38])[CH:34]=[C:33]([C:41]([F:44])([F:43])[F:42])[CH:32]=2)[C:22]2[N:27]=[CH:26][C:25]([C:28]#[N:29])=[CH:24][N:23]=2)[CH2:3][CH2:2]1.[OH-:49].[K+].OO>C(O)C>[CH:1]1([CH2:4][N:5]([CH2:45][CH:46]2[CH2:48][CH2:47]2)[C:6]2[N:11]=[C:10]3[N:12]([C:16]([CH3:17])([CH3:18])[CH3:19])[N:13]=[C:14]([CH3:15])[C:9]3=[CH:8][C:7]=2[CH2:20][N:21]([CH2:30][C:31]2[CH:36]=[C:35]([C:37]([F:40])([F:39])[F:38])[CH:34]=[C:33]([C:41]([F:43])([F:44])[F:42])[CH:32]=2)[C:22]2[N:27]=[CH:26][C:25]([C:28]([NH2:29])=[O:49])=[CH:24][N:23]=2)[CH2:2][CH2:3]1

Participants

5

Reactant 3

HCID 784Hydrogen PeroxideHCID 14797Potassium HydroxideHCID 71539629HCID 71539629, compound

Product 1

HCID 71539628HCID 71539628, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
40 °C

Procedure

2-(((6-(Bis(cyclopropylmethyl)amino)-1-(tert-butyl)-3-methyl-1H-pyrazolo[3,4-b]pyridin-5-yl)methyl)(3,5-bis(trifluoromethyl)benzyl)amino)pyrimidine-5-carbonitrile obtained in Example 10, (0.000074 mmol, 0.050 g) in ethanol was treated with 1% solution of KOH (5 ml) and catalytic amount of hydrogen peroxide. The reaction mixture was heated at 40° C. for 30 min. The reaction mixture was then concentrated under reduced pressure, treated with water and extracted with EtOAc. The organic layer was dried over sodium sulfate, concentrated under reduced pressure, and purified by column chromatography using silica gel and 40% EtOAc in petroleum ether as eluent to obtain the title compound.

Workup

  1. concentrationThe reaction mixture was then concentrated under reduced pressure
  2. additiontreated with water
  3. extractionextracted with EtOAc
  4. dry with materialThe organic layer was dried over sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. custompurified by column chromatography

Sources & evidence

ORD record
ord-f7185b7845ea4241a2f4bceefbf8cac9
Source dataset
uspto-grants-2015_04
Patent number
US09000007B2

Reaction notes

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